What Is a 50 at 50 Challenge — and Why I Did Mine Differently

First, a bit of context. For as long as I can remember, I’ve always done something new on my birthday — made sure I visited somewhere I hadn’t been before, tried a restaurant I’d never eaten in, or did something I’d not yet done. Just the one thing, every year. As a way of making my birthday truly memorable rather than just another year accumulating. We drift into habits so easily, don’t we? But that particular habit — the birthday new thing — brought me real pleasure, genuine joy, and more memorable experiences than I can count.

So when my Mega Tombola birthday arrived (tombola birthdays are the ones that end in a 5 or 0, so naturally they demand a bigger celebration — and 50 is the biggest tombola birthday of the lot), it felt completely natural to expand that idea. Instead of one new thing, why not fifty? One for every year of my life. I’d seen others do similar challenges. Every version I’d come across worked the same way: write the list first, then tick them off.

So that was how I started, but compiling the list simply didn’t excite me — it felt like a chore. Writing a list at one fixed point in time felt too rigid, too task-focused, too removed from the actual messy, unpredictable business of living. I wanted something more heart-led. Something that would push me to say yes in the moments I’d naturally have said no, rather than chasing experiences I’d dreamed up twelve months earlier from the comfort of my sofa and with a background desire to “impress people”.

So my 50 new at 50 list grew as I lived it — and the difference that made to the whole experience is something I really want to talk about, because it changed everything.

The Year That Unfolded with my 50 at 50 challenge

It started gently enough. Number one was a tour of the Oxford Colleges on my birthday itself — 26th January. Number two was buying a sparkly party dress, which I then wore for number three: a gorgeous celebratory weekend away with my favourite people. Lovely. Manageable. Nothing too terrifying.

And then number four arrived, and the tone shifted entirely.

I agreed to be a contestant in Strictly Florence — a local Strictly Come Dancing-style event raising funds for Florence Nightingale Hospice Charity. I’d never had a proper dance lesson in my life. By number five I was in my first ever professional dance class, and by number six I was learning a couples routine. Every rehearsal was a brand new experience in itself: the nerves, the laughing, the sheer concentration of trying to make your body do something it really doesn’t want to do. And then, on 2nd June, number fourteen arrived — performing on stage at the Aylesbury Waterside Theatre in front of a real audience, with real famous judges. I scored two 7s and two 9s. I cried. And I beamed. I was, in the truest sense, PROUD.

Culturally, we don’t really give ourselves permission to say that, do we? It’s acceptable to praise others but somehow uncomfortable to claim pride in ourselves. So I’m going to say it plainly: I went and absolutely smashed it, and I’m not even slightly sorry for saying so.

The unexpected ones

Not every entry was a dramatic set piece. Some were quieter, and in their own way more significant. Number nine was seeing Madame Butterfly at the opera with my mum. I arrived feeling slightly unsure how I’d feel about it and left deciding to simply feel the music rather than trying to understand the words, which turned out to be entirely the right call. Number fifteen was attending my first ever Pride march, and being surrounded by such open, joyful, fully accepting souls was genuinely tender and inspiring. Then, number seventeen was Summer Solstice drumming at Combe Hill with my youngest daughter. Chilled, unhurried, and quietly magical.

Number sixteen made me cry on my walk to work. It was the last morning I’d say my daily school-drop mantra to my youngest: “work hard (her: have fun), have fun (her: work hard), have a good day at schoolious, love you.” That day, officially, I stopped having children and started having a brood of independent young women who’d left education. My middle one had also just got her first proper job and moved into her first flat with her partner. My new experience that day was entering an entirely new phase of motherhood. One I hadn’t seen it coming until it arrived.

The ones that terrified me

Here’s where it gets interesting. Because if I had written a list in January, I know these wouldn’t have been on it.

Number twenty-two was climbing Snowdon — up the Pyg Track and down the Miners’ Path. I cried three times. I didn’t even realise I was scared until my face started leaking on the rocks. Near the summit, my breathing faltered and it felt like my throat was closing. I talked myself through it, kept going without looking at the scary bit. Then on the way down I stopped to congratulate myself for reaching the summit of what had truly terrified me. When I finished, I said — and meant it — “first mountain climbed, will probably be my last.” Reader, it was not my last.

Number twenty-three was the world’s fastest zip wire in Wales, a birthday gift from my in-laws. I very nearly bottled it during the practice run. The fifteen-minute journey up to the top of the mile-long cable involved a lot of positive self-talk, several deep breaths, and at least one moment where I questioned every decision I’d ever made. I did it anyway. The photos are spectacularly unflattering and I posted every single one, because they aren’t there to look good — they’re there to mark the moment I pushed past the fear.

See the video here

Number twenty involved diving off a boat in Sicily for the first time — something I’d always wanted to do but never quite found the courage for. I also jumped off the side of the boat with my youngest, swam into a cave together, and then subsequently had to rescue her from said cave when she was stung by a jellyfish, returning her to the boat with the help of a life jacket and a very kind Australian passenger. I did not get a photo of the dolphins that swam alongside us — that is fine because we don’t need photographs to capture true memories, we hold them in our souls.

The big life ones

By autumn, the challenges had morphed from individual experiences and had started to reshape the rest of the year. Number twenty-eight was quitting my job to visit South America with my partner Ren — not for a holiday, but for a new way of living and working entirely. Think Race Across the World, but without the racing.

What followed was a cascade of firsts I could never have planned. It started in Portugal, walking the entire Fisherman’s Trail — 216 kilometres over twelve days, with 3,453 metres of elevation gain. Learning to play the Italian card game Scopa from Spaniards in a Portuguese café (we’d accidentally bought Scopa cards thinking they were ordinary playing cards — and then the right people appeared at exactly the right time to teach us). Having dinner with a Lithuanian couple we’d kept crossing paths with along the trail, who are now our friends. All the way to travelling overnight by bus across Argentina. Standing in the Andes for the first time. Climbing Refugio Frey at 1,700 metres — more than twice the height of Snowdon! And filling my water bottle from the clearest mountain stream I’ve ever seen.

And then, on 26th January — my 51st birthday, in the southern hemisphere, in a restaurant in Bariloche — eighty people sang Happy Birthday to me in Spanish.

What My 50 at 50 Actually Taught Me

I want to come back to the mountain for a moment, because I think it captures something important. When I stood at the bottom of Snowdon in July and said “probably my last,” I genuinely believed it. Six months later I was climbing something twice the height and loving every step. That shift didn’t happen because I’d put “climb a bigger mountain” on a list. It happened because the experience itself changed me! And because I gave myself the permission and freedom to grow into someone who wanted to do it.

That’s the thing about a list written in advance: it can only reflect the person you are when you write it. It can’t account for who you might become by month eight.

My 50 new at 50 challenge wasn’t really about experiences. It was about acknowledgement — the practice of noticing newness, naming it, and sitting with what it brought up. Fear. Joy. Pride. Grief. Wonder. All of it. At fifty years old, I’d stopped acknowledging the new things I was experiencing. I was still living them, but they were sliding past unnoticed. This year made me pay attention, and paying attention encouraged me to grow in ways I could never have dreamed of, let alone written a list of.

Your Own 50 at 50 Challenge

If you’re thinking about doing something similar — whether that’s 40 new at 40, 30 new at 30, or any version that feels right for where you are — I’d gently suggest you think about what you actually want from it. If the goal is to push yourself to do more, say yes more, try more, or simply love your life a little more, then the list you write in advance might actually get in the way. The best things that happened to me this year were the ones I didn’t see coming.

Let the year surprise you. It’s better that way.

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Are you thinking about doing a new experiences challenge for a milestone birthday? Or have you done one already? I’d love to hear about it in the comments below — did you write your list in advance, or did you let it unfold?

Want to follow the adventure?

You can read about our slow travel journey across South America over on the Slow Across the World series — and if you’d like to read Tanya’s take on milestone birthday challenges, her 40 before 40 list is well worth a read too.